Trail Running calendar near Rosaryville 2026-2027

Experience a mix of twisty singletrack and open farm field running in Germantown. This late autumn trail event offers three distances and a festive post race atmosphere at the historic Button Farm.

Experience a 50 mile trail race through the scenic Seneca Greenway and Muddy Branch trails in Maryland. This event features forested single track terrain and small stream crossings for dedicated distance runners.

Trail 5 km and 10 km races at Burke Lake Park on November 7, 2026, with walkers welcome and virtual entries offering medal and shirt options.

Run Through the Grapevine is an 8K cross country race at Linganore Winery in Mount Airy, Maryland on November 8, 2026. The course runs through vineyard rows and adjacent hop yards, and all finishers receive one free winery tasting.

Trail and virtual runs at Valor Ranch in King George VA featuring timed 10K and 5K events, a 10K ruck, a 1 mile fun run, and 100 percent of proceeds supporting Valor Ranch charitable programs.

A fall trail event at Trap Pond State Park featuring a 4.5 mile loop on the Bob Trail and a 2 mile walk. Participant fees support Legacy Academy.

Looped 50K and 20K trail races at Rosaryville State Park near Upper Marlboro MD, single track woods, two aid stations, drop bag support and military awards.

Trail races at Hemlock Overlook in Clifton, VA offer two loop options, 5.2 miles or 9.5 miles. The course follows hiking trails, dirt roads and fields along Bull Run and includes designated spectator areas and park facilities.

A pre Thanksgiving run at Barrel Oak Winery in Delaplane offering 3K and 6K courses, virtual entry options, and walk and leashed pet access.

A free 5K cross country at Herring Run Park on November 15 featuring mixed surfaces, two river crossings, wooded trails, and donations accepted for local scholarships and park support.

A 25K trail race in Queen Anne, MD on November 21, 2026 featuring single-track and horse trails, three aid stations, and awards for top finishers.

A cross-country 5K and one mile fun run at Ida Lee Park in Leesburg on November 21, 2026, featuring a long sleeve shirt for pre-registered 5K runners and a finisher medal for one mile participants. Donations for Loudoun Hunger Relief are re..

Experience riverside singletrack at Riverbend Park with 5 and 10 mile trail races. This event offers scenic Potomac River views, a dedicated kids program, and professional race support in a beautiful natural setting.

In-person 5 km and 10 km races on the flat Chesapeake and Ohio Canal Towpath at Carderock Park in Potomac, MD, with virtual entry options on November 22, 2026.

A 5 km and 10 km race at The Winery at Bull Run in Centreville on November 25, 2026, with in-person and multiple virtual entry options.

Celebrate Thanksgiving with a cross country style race through scenic Catonsville. Support the local high school running program with a chip timed 5K or a 1 Mile Family Fun Run for all ages.

Thanksgiving morning run at Burke Lake Park offering 5K and 10K courses plus virtual options and a technical shirt guaranteed for registrations before November 13.

Thanksgiving Day events at Sherando Park on 11/26/2026 include a 3.1 mile 5K plus a 100 m Tot Trot and two kids fun runs, each with specified registration windows and fees.

A trail and canal run near Great Falls, Maryland on November 26, 2026 covering about 10 miles with options to shorten. Entry opens November 12 and is capped at 29 runners; entrants receive course instructions before the run.

Trail 5K and 10K in Wheaton Regional Park on November 26, 2026, with virtual options and series points for year-long and fall standings.